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MassachusettsWinchester

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Featured Agents in Winchester, MA

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PRIME AGENT
Deborah Miller profile picture
Littlefield Real Estate

Deborah Miller

Completed Profile
2 reviews
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22years of experience
17sales in the last 12 months
150transactions all-time
Prime Agent Badge
PRIME AGENT
Druann Jedrey profile picture
Leading Edge Real Estate

Druann Jedrey

10 reviews
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19years of experience
22sales in the last 12 months
Victoria Kustov profile picture
Victoria Kustov, Realtor, Elite Realty Experts

Victoria Kustov

4 reviews
View Profile
22years of experience
29sales in the last 12 months

Compare 15 top-performing real estate agents in Winchester, MA

Re/max Andrew Realty Services

The Shawn Sullivan Team

8 reviews
Open 9:00 AM - 5:00 PM
Usually responds in 1 hr
20 years of experience
26 sales in last 12 months
500 transactions all-time
Serves Winchester

About

Shawn- Im a REALTOR/Broker with RE/MAX Andrew Realty Services.I was born in Somerville,I'm a lifelong resident of the Boston North area. My passion for the real estate business began when I purchased my first piece of land and began developing homes.I obtained my construction supervisors license and went on to launch a successful real estate trust firm that specialized in residential development opportunities. Sory- I’m member of The Shawn Sullivan Team born and raised in Brazil. Fluent in English and Portuguese,I’m a REALTORĀ® who built a solid career at RE/MAX Andrew Realty Services prior to joining the team and also been an active presence in local & state REALTORĀ® organizations; as the former vice president of EMAR, recipient prestigious ā€œDorothy M. Shea Awardā€ ,on the state leve I served as a MAR 5 Star Professional Standards Code of Ethics Instructor and a member of various committees such MAR’s Forms and GBAR’s Young Professionals Network .I’m a Certified Military Home Specialist

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Achievements

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Top Listing Agent 2025
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Top Company Agent 2025
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Top Producer 2025

Platinum Award 2021

Business Highlights

1031 Tax Exchange, Buyer Representative, Condominiums, First Time Buyers

Compass

Joelle Smith

9 years of experience
22 sales in last 12 months
Serves Winchester

About

A real estate pro who believes that buying and selling a home is much more than a transaction. Part therapist, part analyst, and expert communicator, Joelle understands that real estate is all about relationships and hers endure long after closing. #clientsnowfriends is her motto, evident in glowing reviews and her repeat business rate. A GREEN and Certified Residential Specialist (CRS) and experienced flipper, Joelle help clients see past the wallpaper and pink carpet. She also leaves no stone unturned when searching for a home for first-time buyers or homeowners needing a change often uncovering off-market and hidden opportunities. Joelle lives, works, and plays in the area and understands the unique charm of each town and the best places and spaces for schools, food, and fun from Boston North to Southern New Hampshire.

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Achievements

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Top Producer 2025
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Top Listing Agent 2025
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Top Buyer's Agent 2025

Chairman's Club 2020, Platinum Award 2019 and 2021, #1 Agent in Office 2019 and 2021, Top 5 individual agent Melrose 2022, Top 25 Agent Stoneham 2022

Bachelor's Degree, University of Wisconsin - Madison
Communications, 1997 - 2001

CRS, GREEN

Joelle Smith's Video

Century 21 Commonwealth - Winchester

Sumi Sinnatamby

31 years of experience
Serves Winchester

About

Sumi Sinnatamby is a Real Estate Agent in Winchester, MA with the brokerage Century 21 Commonwealth - Winchester. Over the last 31 years we have tracked null MLS listings by Sumi.

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Achievements

REALTORĀ®, CRSĀ®, GRI

Business Highlights

Buyer Representative, Condominiums, First Time Buyers, New Construction

Coldwell Banker Realty

Anne Kennedy

Completed Profile
Open 8:00 AM - 7:00 PM
Usually responds in 30 minutes
Prime Agent Badge
PRIME AGENT
10 years of experience
25 sales in last 12 months
144 transactions all-time
Serves Winchester

About

Anne offers seamless, concierge-level support for all her clients, guiding each step with precision and care. She artfully crafts a narrative for every property, meticulously analyzing market trends to position homes competitively and at precisely the opportune moment. Anne's insights transcend the transactional; her keen eye for staging, upgrading, and repurposing becomes a transformative force, elevating property values while diminishing time spent on the market. Anne leverages her formidable arsenal of innovative marketing tools across a myriad of platforms, from captivating online showcases to tailored e-blasts, mailings, and unforgettable open-house events. Recognizing the emotional weight that accompanies selling or buying a home, Anne's grace and expertise ensure a stress-free journey for her clients. Her wealth of experience in construction affords her an intimate understanding of every facet of a home, from the foundation to the roof. See Anne's reviews on Zillow and Google!

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Achievements

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Top Producer 2025
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Top Listing Agent 2025
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Top Buyer's Broker 2025

Real Trends/Tom Ferry Top Producer 2022,2023.Boston Magazine Top Agent 2022, 2023. Coldwell Banker International President's Elite, Top 100 Agent in New England

Bachelor's Degree, University College Cork
Economics , 1982 - 1985

ABR, e-PRO, REALTORĀ®, SFR, GREEN, SRES, CLHMS, Pricing Strategy Advisor

Business Highlights

New Homes, Luxury Properties, Relocation, New Construction
Comparative Market Analysis of your home
Complementary Home Staging services
Single family, Condominium and Multi-family homes

Lina Kriva Homes International |keller Williams Realty Boston Metro

Lina Kriva Homes International

1 review
Open 9:00 AM - 7:00 PM
Usually responds in 1 hr
Prime Agent Badge
PRIME AGENT
19 years of experience
14 sales in last 12 months
133 transactions all-time
Serves Winchester

About

Our Art is Real Estate! We work with you through every step of the process negotiating the complexity of the deal and maximizing your profit to a successful transaction. We look forward to being your real estate resource now and in the future.

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Achievements

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Top Luxury Buyer's Agent 2025
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Top Luxury Listing Agent 2025
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Top Sales Producer 2025

Master's Degree, UM - Carlson School of Management
A

Lina Kriva Homes International 's Video

We've introduced over 4,940,482 buyers and sellers to top local real estate agents in the past 15 years

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Winchester Housing Market Report

Market Action Index

We are extensively tracking the housing market in Winchester, MA. Here are the strongest factors contributing to this score:

The median prices are rising year over year
Fewer sellers are listing their homes compared to last year
100
seller's market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$2.35M

Per Square Foot

$559

Days on Market

65

Total Listings

44

Median List Price

Mon, Apr 13, 2026

Median List Price
1 Year

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